


So When Do I Get To Pledge My Loyalty To The Mob?

by RedRidingStiles



Series: Sterek Shorts [5]
Category: Teen Wolf (TV)
Genre: Aged-Up Character(s), Alternate Universe - College/University, Alternate Universe - Mob, Alternate Universe - No Werewolves, Bad Friend Scott McCall (Teen Wolf), College Student Stiles Stilinski, Confusion, Derek Hale Needs To Use His Words, Derek is in like one scene sorry, Erica Reyes & Stiles Stilinski Friendship, First Meetings, For A Good Cause, Getting Together, Gifts, I Wrote This Instead of Sleeping, M/M, Mob Boss Derek Hale, New York City, Rich Derek Hale, Sleep Deprivation, Stiles Stilinski & Jackson Whittemore Friendship, Stiles Stilinski Works Too Hard, Stiles Stilinski is a Mess, Sugar Daddy, slight stalking
Language: English
Status: Completed
Published: 2019-01-29
Updated: 2019-01-29
Packaged: 2019-10-18 14:24:44
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 10,089
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17582561
Author URL: https://archiveofourown.org/users/RedRidingStiles/pseuds/RedRidingStiles
Summary: “Are you my sugar daddy?” Stiles blurts out, slapping a hand over his mouth when his brain catches up to his mouth. The man lets out a soft laugh, making his way around the couch till he’s standing just feet away from Stiles. Stiles can smell his cologne from here, it smells heavenly, Stiles kinda wants to bury his face into the guy's chest so he can figure out exactly what it is.“If that’s what you’d like to call it.” The man smiles, Stiles doesn’t think he should be allowed to smile like that. All soft and gorgeous and way too pretty to be legal. He’s still not convinced any of this is real.Stiles loses his wallet, someone returns it along with $5,000. Shit keeps coming, Stiles life doesn't make any sense anymore, he's just going with it.





	So When Do I Get To Pledge My Loyalty To The Mob?

**Author's Note:**

> Tumblr prompt I saw: One day you lose your wallet, and it's found by a mob boss, who figures out that you aren't in such a good place financially and takes pity on you. So they start anonymously sending cash, clothes, and furniture to you in the mail. Eventually, the mob boss sends you a letter saying they bought you a house and it list an address, what do you do?
> 
> In this economy? Thank them politely, pledge your loyalty, and join the mob.

[Stiles](https://www.pinterest.com.au/pin/628674429207876359/)

 

[Derek](https://www.pinterest.com/pin/814166438864018389/?lp=true)

 

Exhaustion was something Stiles was used to by now, in high school he’d pull all-nighters by popping a couple Adderall and drink half a pack of red bull to finish assignments he spent way to much time on perfecting. When he got to college he went five days on three hours of sleep during freshman year finals trying to cram in as much information as he could. When the life insurance money he had from his mom ran out in his junior year he got a job at a shitty diner and later picked up shifts at an upper-class bar to pay the rent for his hole in the wall apartment he shared with his friend Scott.

So yeah, he's used to little sleep and unhealthy amounts of caffeine. It was just the way his life was by now, being in the city that never slept seemed only too fitting for him. Stiles had been getting by pretty well, his dad worried but that was to be expected since they were all each other had left. But it was okay, he was doing fine, sure money was tight and he can’t remember when the last time he slept more than three hours at a time was but he was getting his degree. He lived with his best friend and got to be a part of the hustle and bustle of the big apple. His life was going decently for a 21-year-old college student in this day and age, until everything seemed to go to shit.

“What do you mean you’re moving out?” Stiles had just gotten home from his evening shift at the diner and had less than an hour to shower, change and catch the train uptown to get to the bar on time for his shift.

“Allison is transferring to Stanford to be closer to her family and I’m going with her, I can finish vet school there and her and I can finally move in together.” Scott explains as he packs his clothes into boxes in their shared bedroom. They had only just had enough money for a one bedroom that was close enough to the school and their jobs, only just enough because Scott was able to pay his share from working at the local vet’s office part-time and the money his dad sent him to make up for being a shitty parent.

“So you’re just leaving? Without even talking to me about it?” Stiles cannot believe this shit right now, he’s running on six cups of coffee and three red bulls and a grand total of 40 minutes of sleep he got last night. Not to mention this is the first time he’s seen Scott in almost three weeks, ever since Scott started dating Allison two years ago it was like Scott had completely forgotten about Stiles. With Stiles’ ridiculous work schedule and the two were basically strangers. When Stiles did have time off and tried to get Scott to hang out he always brushed him off and said he had plans with Allison already.

“Look dude, I love Allison and I want to be with her, I’m not leaving right away. We found a place already but we can’t move in till after the semester is over.” Scott sighs, clearing off the dumpster desk they saved three years ago.

“So what, I have two weeks to find someone who can pay the other half of the rent? Someone who wants to share a one bedroom flat with a complete stranger? I cannot fucking believe you right now, man!” Stiles huffs in anger, tugging on the ends of his hair. There was no way he’d be able to find someone who wasn’t a creep or serial killer who would want to share a bedroom with him.

“I can still pay next month’s rent so you have a little more time, I know this is hard for you dude-” Stiles tunes out the rest of what Scott says, livid that his best friend of 13 fucking years was dropping him on his ass for a girl he met two years ago. Some fucking best friend.

“-And Allison lives with three other people so she doesn’t have a lot she can take with us so I was thinking since we bought most of the furniture together we could go through and pick out what we each want.” Scott finishes, Stiles really only catching every few words but still enough to understand what he’s trying to say.

“I can’t fucking deal with this right now.” Stiles sighs heavily, shaking his head and ignoring Scott calling his name as he goes into the bathroom and slams the door.

Stiles can feel the anger and betrayal and panic creeping up on him and he doesn’t have fucking time for this shit. He has to be at work in 30 minutes and the next train leaves in 15. He takes a quick shower to scrub the smell of grease and coffee off of his skin before throwing on his nicest button up that Lydia says makes his arms looks good and the pair of jeans he grew out of a year ago that hug him just a little too tight. He needed to make money tonight, would need to find another job or pick up even more shifts once the semester was over if he wanted to pay the fucking rent once Scott had fucked off. He threw on some cologne and popped two Adderall to keep him awake before he heads out, completely ignoring Scott when he tried to talk to him.

The bar is already busy when he clocks in, it’s ten on a Saturday and he’s bartending with his manager Erica tonight. Stiles stashes the red bull he brought with him under the bar and throws a towel over his shoulder, plastering on a winning smile for the people lounging by the bar as he moves to greet Erica.

“Good, you’re finally here, once we slow down a little I have to do some inventory because fucking Matt didn’t remember to last night so I’m going to be in the back for a while. You okay with watching the bar by yourself?” Erica starts before he can even open his mouth, handing a drink to a nicely dressed man with a flirty smile, her cleavage on full display.

“Yah I can handle it, but I wanted to ask you real quick if there were any shifts I could pick up during the summer.”

“I’ll have to look at the scheduled but I might be able to add you in more, Heather is going on vacation for a week or so after the term ends. Are you still working the diner?” Erica replies as she mixes up a martini, one perfect eyebrow raised in question.

“Yah I am but Scott fucking McCall decided he wants to abandon me and take half our furniture when he leaves me in the dust to go live with his girlfriend in California.” Stiles spits, his hands shaking at his side with rage. Who was he kidding, it was probably from lack of sleep and too much caffeine then it was the rage.

“What a fucking asshole, how are you going to pay your rent?” Erica growls which makes Stiles feels pleased that he’s not the only one who thinks Scott is being a shitty friend. Stiles understands wanting to be with your girlfriend and all that shit but why not talk to Stiles beforehand? Who drops a bomb like that and only gives two weeks notice?

“I’m going to have to pick up more shifts and probably find a third job.” Stiles sighs, walking away when a cluster of young women flag him down. He flirts while he takes their order, winking as he goes to make their drinks and hoping to God they tip well.

“You could always try stripping,” Erica shrugs as he fires up the blender for the margaritas.

“Please, as much as I wish I could, I don’t have the coordination for that.” Stiles snorts with a roll of his eyes.

“Got the ass though,” Erica teases, giving him a hard slap and a wink when he doesn’t even flinch.

“What about an escort? You’re good with people and it pays really well if you go through the right company.” Erica suggests as Stiles pours his drinks.

“Are you trying to pimp me out? Or do you just wanna get me in bed and are trying to hint to me?” Stiles asks with a smirk, putting little umbrellas in the drinks before taking them over to the ladies waiting for him. They pay in cash and leave him a ten dollar tip and one of their phone numbers, Stiles might have to have Erica slap his ass some more if the results would be the same as this.

“Hey, I offered when you first started working here and you turned me down.” Erica huffs, passing a beer to a man sitting down in the middle.

“Because you have a boyfriend that is literally twice my size!” Stiles cries, getting a wicked smirk in return.

“I thought that was your type?”

“Hey, everyone likes to be manhandled every now and again but I am definitely not Boyd’s type.” Stiles states with a shake of his head, pulling out his red bull and drowning a third of it before he goes to take another order.

“When was the last time you got laid?” Erica questions bluntly, raising her eyebrows when Stiles has to actually think about it.

“Uh, winter break, maybe? I think that was just a blowie through.” Stiles hums, ducking his head with a smirk when he sees several eyes lingering on him as he says it. Stiles works at a bar, he gets offers to go home with men and women almost every night but he doesn’t have the time for anything like that.

“You need some dick, or need to give some. I can’t believe it’s been that long.”

“I don’t really have a lot of time for anything like that, least of all right now, not with this shitstorm Scott just kicked up.” Stiles sighs handing a round of shots to a couple that walked in a minute ago.

“I’ll get you more shifts, hun, promise.” Erica squeezes his shoulder in comfort, her face soft as he smiles up at her.

“Thanks, Catwoman.”

“Anything for you, Batman.”

 

 

 

***

 

 

 

Stiles ignores Scott for the next week, working double and triple shifts, sleeping even less than usual as he tries to cram for his last two finals in between work. He’s got a shift at the bar again tonight and he’s just glad it’s not with fucking Matt because that guy is not only a huge asshole but also one of the laziest bartenders he’s ever met. He’s getting dressed when Scott comes into the room, a notebook in hand as he stands in the doorway, blocking Stiles’ escape.

“What?” Stiles bites out as he shrugs on his red scoop neck shirt, his collarbones on full display.

“I made a list of all the furniture and marked what would be good for Ally and I to take with us, I wanted you to look it over,” Scott says as he holds out the notebook to Stiles. Stiles rolls his eyes hard and takes it after he’s slipped on his shoes, reading it over quickly. His knuckles turning white from how hard he’s holding the notebook. Scott had basically circled everything but the shit couch and desk in their room.

“You know what? Why not just take everything? Who the fuck even cares, it’s not like I need anything more than a fucking bed I never sleep on and a desk to do my work on.” Stiles hisses, throwing the notebook harshly in Scott’s direction as he grabs his phone, keys, and wallet. “I don’t even fucking care anymore, take whatever you fucking want, it’s not like I’m ever fucking home to use it.”

“Stiles-” Scott starts to say as Stiles shoves his way past him, heading for the fridge for a few red bulls for tonight.

“Don’t. Just-just fucking don’t.” Stiles growls, slamming the fridge shut and stalking towards the door.

“Do me a favor McCall,” Stiles calls out as he opens the door, glancing back to see his so-called best friend standing in the middle of the living room, the notebook dangling in his hand. “Lose my number when you finally fuck off.”

Stiles feels a sort of peace when he slams the door, his life might be going to shit, he might not have slept in the last three days, but at least one shitty thing is getting dealt with. Stiles kind of feels like it’s been a long time coming, almost two years overdue.

 

 

 

***

 

 

 

“You can’t be fucking serious.” Stiles mutters to himself as he pats his pockets looking for his wallet. It’s been a week since Scott and Allison moved to Stanford, taking everything in the living room and all of Scott’s shit with him. The only thing left was Stiles twin sized bed, broken desk, wobbly chair and the dresser he had found on the side of the road a year ago.

“This is not happening.” Stiles hisses when his search comes up empty. It had been a long fucking day, he had worked the early morning shift at the diner and picked up a double at the bar. It was 3:30 in the fucking morning and he has lost his fucking wallet. He hadn’t realized till now because Erica had given him a ride home so he wouldn’t have to take the subway.

“What am I doing with my life?” Stiles groans loudly, collapsing down onto his tiny bed with his hands covering his face.

School had ended which was a silent miracle but Stiles had found another job at a bakery four blocks down that he started at tomorrow. He had worked it out with each of his bosses, work 4 to 9 at the bakery on weekdays, 10 to 8 at the diner four times a week and 10 to 3 at the bar almost every day of the week since Matt had been fired and Heather had asked for another week off. He was working his ass off with 95 to 100 hour work weeks and his paychecks and tips were enough to pay the rent and utilities and still leave him enough to put towards his savings for when school starts back up but he wasn’t sure how long he would last once school started up and he’d have to cut all his hours in half.

He was going to be averaging an hour and a half of sleep per day when he worked all three jobs and had told Erica he could pick up more at the bar on the days he didn’t work at the diner and was already scheduled for two double shifts this week. Now he was going to have to use the tip money he had stuffed in his hoodie pocket to get a cab to the diner and the bar tomorrow. He could walk to the bakery but the diner and the bar were half an hour away in different directions.

“Fucking _Scott_ ,” Stiles curses into the silent apartment, rubbing at his tired eyes in frustration. If Scott hadn’t ditched him with a two-week notice he would only be working two jobs with reasonable hours and actually have time to sleep more than an hour at a time. He wouldn’t have to worry himself into a panic thinking about what he was going to do once school started up again.

“Fucking shit,” Stiles grumbles as he peels himself off the bed and changes into some loose jeans and a crappy tee for his shift at the bakery. He made a quick cup of coffee and didn’t bother to put sugar or creamer in it, transferring it to his to go cup and walking out the door to make his way to the bakery where his new boss was waiting to train him.

 

 

 

***

 

 

 

Stiles was dead on his feet when he got home from the diner, he had gone straight there after finishing at the bakery so he could get a quick meal and drown a ridiculous amount of coffee before his shift started. He’d gotten a half hour dinner break that he used to nap in his bosses office since she had left for the day which turned out to be a mistake since it only made him feel even more tired. He hadn’t even gotten the time to call his bank and freeze his debit and credit cards, glad he had only had 32 dollars in his wallet when he had lost it.

Stiles grabbed the mail after getting out of his cab, rifling through it with his bloodshot eyes, growling at anything addressed to Scott as he unlocked his front door only to step on something in the middle of the doorway when he gets inside his apartment. Frowning he looks down to see a yellow messenger envelope sitting on the ground.

“Weird.” Stiles mutters to himself as he picks it up, moving to the kitchen and dumping the mail onto the counter and tearing open the envelope.

“What the fuck?” Stiles gasps as he pours the contents onto the table, his eyes wide as he looks down at his wallet and a small stack of crisp 100 dollar bills. There’s a little post-it note attached to the bills, small neat handwriting in blue ink staring up at him.

_‘Get some sleep and there’s more where this came from. -D’_

“ _What the fuck_?” Stiles repeats breathlessly, racking his brain for anyone he knows with the first initial D, he can’t think of anyone that would send him money let alone this much. Stiles picks it up gingerly, almost afraid to touch it but wanting to know how much is there. He counts it quickly, then recounts it and repeats it two more times just to make sure he’s not seeing things in his sleep-deprived state.

“Who in the fuck would send me 5,000 dollars?” Stiles asks the empty room, dropping the bills back onto the counter and running a hand over his face, trying to get his thoughts together. There was more money sitting on his counter then he made in a month, this plus the money Scott left for the rent was enough to pay two months rent. He already had enough money to pay the first two months rent for the summer which meant if he kept up with his schedule he could stash away his next few paychecks to get his savings up for when senior year started. He looked down at the note, rereads the message with a yawn before deciding he could sleep for a little over an hour before his shift at the bar.

 

 

 

***

 

 

 

The next week went by slowly, days dragging on and on with only a half hour here and an hour there of sleep. His three days off at the diner were Friday through Sunday but he had picked up doubles at the bar on Friday and Saturday and had been looking forward to sleeping the day away on Sunday when he only had to work the bar at night.

Stiles ended up only getting six hours of sleep though, his mattress lumpy and the sunshine streaming in through the windows making it impossible for him to stay asleep no matter how hard he tried. That didn’t stop him from only leaving his bed to go to the bathroom twice and getting food once around one. Stiles laid in bed dicking around on his phone and calling his dad to check in.

Stiles showered an hour before he had to be in, taking his time to get dressed for once and wishing he could hash out some money for some better fitting clothes, knowing he couldn’t if he wanted to save as much as possible.

“Hey Catwoman,” Stiles greets when he enters the bar, Sunday’s weren’t that busy and Erica only had an hour left of her shift before she got to head home, leaving Stiles to close up by himself.

“Lookin’ good Batman, did you finally get some sleep?” Erica asks, kissing Stiles on the cheek when he gets behind that bar.

“I got a whole six hours, give or take.” Stiles shrugs as he throws a towel over his shoulder, nodding in hello to the few people sitting at the bar.

“Six hours? You had a whole 17 hours off, I thought you would sleep the entire time!” Erica replies, hitting him in the shoulder lightly.

“Hey, I would if I could, my mattress is shit and my good curtains got taken in the divorce.” Stiles huffs back, waving away the worried look on her face.

“Stop, I’m fine, that's more sleep than I’ve gotten all week.” Stiles snorts as he wipes down the bar to give himself something to do. It had been nice to have a day off but had also left him feeling a little lost, he was so used to being on the move constantly.

“Stiles, that’s not healthy, you need to get more sleep. I know you need the money,” Erica clasps a hand over his mouth when he goes to protest. “But I’m not going to give you more than one double from now on. You need to take care of yourself.”

“What I need is to not get thrown out on the street or starve to death because I can’t pay my bills.” Stiles replies sourly once he had pried her hand off his mouth.

“Just...I worry about you, Batman.” Erica sighs softly, her hazel eyes round and her red lips pouted out. Stiles pulled her into his side, hugging her close and dropping a kiss onto her head.

“I know Catwoman, I’m fine though, really. Nothing I’m not used to.”

 

 

 

***

 

 

 

“Ughh, are you fucking serious right now?” Stiles groans when the pounding on his door stirs him from his restless sleep. He has Tuesday and Thursday off at the diner this week, having given up his Sunday when his coworker had asked if he could take her shift so she could go to her son’s soccer tournament.

“I’m coming!” Stiles yells when the knocking starts up again, pulling on a random shirt as he pads his way to the front door.

“M-Mieczyslaw Stilinski?” The man asks, butchering his first name so bad that Stiles cringes to himself.

“That’s me,” Stiles nods, a clipboard being shoved into his hand a second later.

“Sign here.” The man directs as Stiles looks at him in confusion.

“I didn’t order anything.”

“Well someone did, instructed me to give you this.” The man grunts, fishing in his pocket and pulling out a small envelope that he holds out to Stiles.

“Where’s the bedroom?”

“Uh, through that door,” Stiles mutters, waving a hand as he looks down at the letter. The man shouts down the hallway for someone to bring it in, whatever ‘it’ is.

“Woah,” Stiles whispers as two men come in holding a large bed frame, two more following with the mattress and another with a headboard. They head into his room and he hears them moving around his little twin bed, shoving it out of the room as they set up the new bed.

Stiles rips the letter open as the original delivery man comes back in with a large duffle set complete with sheets, new pillows, and a blanket all in a nice light blue and white pattern.

_‘Hope this helps you sleep better, don’t overwork yourself. -D’_

“Who the fuck are you?” Stiles whispers as he pulls out the money enclosed in the envelope, counting it quickly and double checking to make sure he had got it right. 5,000 dollars, all brand new 100 dollar bills, just like last time.

Stiles walks towards the bedroom after shoving the money and note back into the envelope and hiding it in the kitchen. The delivery men were already done connecting the bed frame to the headboard and were getting ready to lay the mattress down.

“Curtains are in with the rest, we’ll take the old bed and junk it when we leave.” The first guy says, motioning to where he had set down the blanketing.

“How-how much did this cost?” Stiles questions cautiously as he stares at the bed, it’s fucking huge, taking up most of his tiny excuse of a bedroom and looking completely out of place.

“A pretty penny, that’s the best mattress we sell and the sheets are Egyptian cotton. There’s a remote that you can use to change the settings of the mattress and the curtains are blackout.” The guy responds, looking at Stiles with a raised eyebrow.

“Do you know who sent it?” Stiles asks, running a hand through his hair as he lets out a shaky breath. This was a lot, way more then Stiles was comfortable taking no matter how nice it was. Stuff like this didn’t just happen, especially not to someone like Stiles.

“No, your name was the only thing that was given along with the cash, address, and letter.” The guy says with a shake of his head. Stiles nods once, the others had finished up and moved to the living room where they were grabbing Stiles’ old bed. Stiles lets them out afterward, closing the door softly before turning around to stare into his bedroom where his new mattress, sheets, and curtains sat.

“What the fuck is going on?” Stiles whispers into the air, his gaze never leaving the bed.

 

 

 

***

 

 

 

The bed was like a cloud, like seriously the softest thing Stiles had ever had the pleasure to touch let alone sleep on. Stiles had walked to the bank after the bed had been delivered, putting most of the money in his savings account but leaving a few hundred out so he could stock up on groceries and more red bull. When he got back home he hung up the curtains and dressed the bed in the sheets before passing out for a whole nine hours. It was the best sleep Stiles had gotten in years, not to mention the most he’s gotten in who knows how long. When he woke up he felt like a new person, the bags under his eyes were still bad but his eyes were no longer bloodshot and his skin actually had some color to it for once. Stiles got ready for work with a spring in his step, humming to himself as he walked to the subway station.

Stiles tried to figure out who D could be as he rode the train, he scrolled through his facebook, Instagram, and even snapchat looking at anyone that first name started with D, only to come up with no one plausible. Stiles knew a decent amount of people, had half of Beacon Hills in his friend list along with all the people he’s met in college or from work but not one of them had the means or motivation to send him 10,000 dollars or a new bed.

He hadn’t told anyone about the anonymous sender, didn’t know how they knew his bed was shit and Scott had taken the curtains in their room when he left. Stiles had only told Erica about that and he knew she didn’t have the money to be getting him these types of gifts.

 _Gifts_. They were gifts, the money, the bed, the curtains, the little notes.

“Oh my God, do I have a sugar daddy?” Stiles whispers in revelation, ignoring the older women side eyeing him two seats down.

Can someone have a sugar daddy and not know them? Stiles is pretty sure a sugar daddy is meant to get something out of the relationship like sex or arm candy or something. Maybe he had a fairy godmother, that seemed more likely, sort of.

“Nothing makes sense, absolutely nothing.” Stiles huffs as he makes his way out of the train and up the stairs, his hands stuffed into his jacket pockets.

“Maybe I have a really rich stalker that’s planning my kidnapping? That seems more likely,” Stiles snorts with a shake of his head, letting out a puff of breath as he rounds the corner to the back entrance of the bar.

“Holy shit Stiles, why do you look so hot?” Erica asks as soon as she catches sight of him.

Stiles frowns because 1) he likes to think he always looks hot when he comes in 2) Erica is making it sound like he never does and 3) He didn’t really do anything that different today. Sure he had styled his hair with gel and wore his tightest v-neck henley and black skinny jeans but he’s worn this outfit to work before.

“What are you talking about?” Stiles questions as he comes to stand by her side. The bar isn’t that busy, Tuesdays hardly ever are but there’s a decent size crowd.

“I’m talking about the fact that you’re fucking glowing, your eyes aren’t red and you don’t look like a zombie for once in your life,” Erica replies, her eyes looking him up and down with what Stiles thinks is pride or maybe lust.

“Uh, well I slept for nine hours so that probably helped and I ate actual food for once.” Stiles shrugs, someone holding up their beer in a silent ask for a refill.

“Sweetie, you need to sleep like that more. I hardly recognized you when you came in.” Erica says as Stiles grabs the guy his beer, popping the tap and sliding it over.

“Don’t get too used to it, I’m working 20 hours tomorrow and Friday and I picked up Sunday at the diner.”

“Stiles, you can’t keep doing this to yourself,” Erica huffs crossing her arms over her chest, making her breast pop out.

“Money Erica, money makes the world go round.”

“When was the last time you did something fun? Or bought yourself something other than a pack of red bull or coffee?” Erica questions, pouring a scotch for the man who sits down in front of her.

“It’s not like I don’t want to, most of my clothes are from high school and barely fit anymore, this shirt,” Stiles pulls at the fabric lightly. “Use to be two sizes too big when I was a freshman. Sure I’d love to do something fun or get myself something but I can’t right now. Everything I make in the next few months is getting put away so I don’t end up homeless when school starts back up.”

“Have you thought about getting a new roommate?” Erica asks, her mouth set in a frown.

“Who’s going to want to share a one bedroom flat with me? Scott took the entire living room and half the bedroom. I literally have a bed, a broken desk, and a shit dresser to my name right now.” Stiles replies, trying not to let the anger get to him. He knows Erica is just trying to look out for him but there isn’t a lot he can do with the situation.

“If I ever see that fucker, I swear I’m going to string him up by his dick,” Erica growls, making Stiles smile slightly.

“You’re a good friend, Catwoman,” Stiles mutters, making the girl roll her eyes as she flips her long hair over her shoulder.

“Of course I am, you’re lucky to have me in your life.”

“Don’t I know it.” Stiles chuckles.

 

 

 

***

 

 

 

Stiles is getting ready to head to the grocery store Thursday morning when there’s a knock on the door. Stiles buttons up his jeans quickly before heading to the door, a nervous feeling in his stomach as he slowly pulls it open.

“Got another delivery for you.” The guy from Tuesday, Stiles doesn’t see a nametag, says as he hands Stiles the clipboard in his hand and waves the people behind him into his apartment.

“Um, what’s going on?” Stiles questions when two women come in wheeling a portable clothing rack filled with clothes between them.

“Here,” The guy says, handing him an envelope identical to the last one. Stiles gently breaks the seal, leaving the money he sees sitting there so he can read the note.

_‘Thought you might like a change of pace, pick out anything you want. -D’_

“Uh, I’m-are those all in my size?” Stiles finds himself asking. He doesn’t even know what size he wears now, hasn’t bought clothes for himself since sophomore year of college and if D knows his size he’s going to be a little freaked out.

“We were told to bring a few options, we’re going to take your measurements and see what would be best. Once you pick out what you like we’ll have it delivered tomorrow evening.” The blonde women replies as she pulls out a measuring tape from her handbag.

Stiles didn’t know what to say, his brain felt like it had been turned on autopilot as the two women took his measurements and wrote them down, lifting his arms when he was told and turning when he was instructed. They handed him clothes and told him to try them on so he did, spending two hours dressing and redressing, the two women, Liz and Gabby, asking his opinion on everything he tried on. Wes, the delivery man, stood off in the corner on his phone waiting while Liz made a list of everything Stiles liked, Gabby handing him outfit after outfit until he had tried on everything they had brought. The fabrics felt expensive and judging by the labels in some of them he was right to assume they were.

“That looks fabulous on you.” Gabby gushes when he pulls on the red and black leather [jacket](https://www.farfetch.com/shopping/men/dsquared2-panelled-jacket-item-13413274.aspx?storeid=9068).

Stiles looks himself over in the mirror attached to the rack, the jacket fit him well, the black sleeves hug his arms but not tight enough to be restricting. There were two large black pockets and another zipper pocket over the left side. The body of the jacket his favorite shade of red. He looked good, really good.

“We’ll leave that with you, everything else needs to be ordered in your size,” Liz states as she looks over her list.

“Um, what all did you write down?” Stiles questions the girl.

“Red is definitely your color so there are three shirts and that button down you like, six pairs of jeans, two regular, two in black, one in gray, and one in white. A denim jacket, a few plaid shirts, regular tees, and three pairs of shorts, all in different colors.” Liz lists off. “Oh and five pairs of shoes.”

“Right, um, how much is this all going to cost?” Stiles coughs, feeling a bit overwhelmed if he was being honest with himself.

“Don’t worry about it, we’ve been told where to send the bill once you had picked everything out,” Gabby says with a dismissive wave of her hand.

“Who? Who’s paying for it?” Stiles questions, needing to know who had taken it upon themselves to do all of this for him.

“We were told not to say anything, they prefer to stay anonymous.” Liz supplies, giving him an apologetic smile.

“Course,” Stiles sighs, running a hand over his face. “Well, thank you for all your help.”

“We’re happy to help, your things are on rush order so they should be here no later than the day after tomorrow,” Gabby tells him as they pack up their things. Stiles watches them leave, waving goodbye to the girls and Wes until he’s alone in his apartment once again.

“Definitely a sugar daddy.” Stiles sighs to himself as he reread the note, counting the money, another 5,000, before heading out to take it to the bank and finally do his grocery shopping.

 

 

 

***

 

 

 

His new clothes get delivered Saturday while he’s at the diner, Stiles brings them inside and hangs everything up, picking out the new dark red button [down](https://www.farfetch.com/shopping/men/dolce-gabbana-classic-slim-fit-shirt-item-13072235.aspx?storeid=9620) and black skinny [jeans](https://www.farfetch.com/shopping/men/ksubi-distressed-slim-fit-jeans-item-13240161.aspx?storeid=9058) for the bar tonight. Stiles takes a quick power nap before he has to start getting ready, showering and eating some cold pizza before he gets dressed. The shirt fits him perfect, as do the jeans and black lace-up [boots](https://www.farfetch.com/shopping/men/lacoste-lace-up-boots-item-13213881.aspx?storeid=10136). Stiles rolls the arms of the shirt up to his elbow, putting a bit of gel into his hair before grabbing his leather jacket and heading out the door.

Erica isn't scheduled today, instead the new guy, Jackson, is working when he steps into the bar. Stiles had worked with him once so far. Jackson had started on Thursday, training under Erica to learn the ropes. He hadn’t needed much training since he had worked as a bartender before so he was already capable of handling things on his own. Stiles didn’t mind him, Jackson was a bit of an asshole but so was Stiles. They had gotten to know each other a little bit the other night and Stiles was actually a little excited to get to work with him again.

“Yo,” Stiles greets the other man as he slips behind the bar, fixing his shirt sleeves as he does. They had come loose when he had taken his jacket off to hang it in the office.

“What the fuck? I thought you were a college student?” Jackson replies as his sharp blue eyes run over Stiles’ body.

“Uh, I am,” Stiles says in confusion, his eyebrows pulling down.

“That’s a Dolce and Gabbana shirt that cost over 400 dollars. Those jeans,” Jackson points down at the black jeans covering Stiles’ legs. “Are Ksubi and are over 200 dollars and those boots are fucking Lacoste by the looks of them.”

“How do you know the brands?” Stiles questions, feeling a little sick at the thought of how much money D had spent on his new wardrobe.

“I’m a fashion major, I live for that shit. How the fuck are you affording all that?” Jackson demands, customers trying to wave both of them down. Stiles goes to help a group of older gentlemen as he tries to think of something to say, he did not want to tell Jackson some random person was sending him thousands of dollars, clothes, and furniture. He also didn’t know if any excuse he came up with would work.

“They...I-I didn’t know they cost that much. They were a gift.” Stiles admits, sighing heavily when Jackson looks at him with two perfect raised eyebrows.

“Who are you fucking?”

“ _What_? No one, I haven’t had sex in like seven months!” Stiles responds, a little loudly he will admit but he really doesn’t want his new coworker thinking he’s some kind of rent boy or something.

“First off, that’s fucking sad you need to get laid, second, who would buy you designer brands if you’re not even fucking them?” Jackson retorts, setting two beers and a scotch down for three regulars that are looking between the two of them in amusement.

“I don’t know okay! Someone just keeps sending me shit I need like some kind of fairy godmother! I don’t even know how they know half the shit they do!” Stiles groans back.

“What else have they sent you?” Jackson questions as he pours a round of shots for the three middle-aged women dressed in skimpy dresses.

“A fucking huge ass bed, rent money, and a new wardrobe,” Stiles replies honestly, trying to keep his voice down so the patrons won’t hear him.

“Sounds like a sugar daddy, do you seriously have a sugar daddy that you haven’t even met?” Jackson snorts, shaking his head in amusement. Stiles does not appreciate this conversation.

“It’s not a sugar daddy, the definition of a sugar daddy is a rich guy that lavishes gifts on a young woman in return for her company or sexual favors. I looked it up, I’m not a women and I sure as hell haven’t been giving sexual favors to anyone.” Stiles huffs in frustration, making Jackson laugh, the ass. Stiles takes it back, he’d much rather have been scheduled with someone else.

“So some random person is just throwing money at you? Why would they do that?”

“I don’t fucking know!” Stiles cries, making the three men watching them snicker into their drinks.

“Maybe they have a crush?” One of the men says, getting an elbow in the side from one of the twins with him. Stiles had seemed them all in here a lot over the past month or so but had never learned their names.

“ _Isaac_ ,” The twin that elbowed the curly haired guy, Isaac apparently, hisses in warning.

“What? You never know.” Isaac smirks behind his glass of scotch.

“So you’ve got a stalker?” Jackson voices, sliding two beers to a couple sitting at the end of the bar who nod in thanks.

“I think I prefer the term sugar daddy now that I think about it, a little less creepy that way.” Stiles snips, getting a sharp laugh from Isaac.

“So they just send you shit? Whatever you need?” Jackson presses.

“Kinda, I told you about my roommate fucking off to the other side of the country right?” Jackson nods in reply. “Well, he took like most of the shit in our apartment and left me high and dry and ever since then shit started showing up after I lost my wallet.”

“You should test it, see what they’ll buy for you,” Jackson suggests, refilling Isaac’s glass.

“What do you mean test it? I don’t even know how they know so much about me.” Stiles rebuttals, the thought making him feel more than a little lost.

“What do you want? If you could have anything what would you ask for?” Isaac questions, the twins glaring at him for some reason.

“I-I don’t know? I wish I didn’t have to work three jobs just to pay for a shitty apartment I barely use, I wish I could just focus on my last year of school instead of worrying about how I’m going to make ends meet when term starts. I wish I could actually take time off and go see my dad without it crippling my bank account. I wish I could actually have a fucking life.” Stiles rants, his heart aching a little as he speaks. He’s been running himself ragged for years now and it was catching up to him.

He doesn’t remember the last time he had a full day off, he hadn’t seen his dad since last summer. Hadn’t gone out and had fun in over half a year. The only friends he talked to were his coworkers Erica and now Jackson. He just wants a break from it all, wants to do something that doesn’t revolve around making money. He wants purpose in his life.

“If money wasn’t an issue, what would you do with your life?” Isaac asks, his eyes trained on Stiles’ own.

“I’d get my doctorates for starters, open my own tech business and actually do what I want with my life instead of working it away.”

“Doctorates? More than one?” One of the twins asks.

“Yah, I’m double majoring right now in business and computer science.” Stiles supplies with a shrug. It was a heavy workload but it’s what he wanted to do with his life. He wanted to expand his schooling but the scholarship he applied for wouldn’t cover enough of his tuition and he was already trying to pay off the student loans he had for the first four years, adding another four wouldn’t do anything but pile more bills up.

“Damn, so if rent wasn’t a factor you’d have time for more than work? Like meeting people and shit?” Isaac presses, making Stiles scrunch his eyebrows together.

“Duh, if this sugar daddy wanted to buy me my dream house and pay for my schooling I’d probably marry them on the spot.” Stiles laughs at his own words, rubbing his hand over his face. Yah that would be the day.

“What’s your dream house?”

“Isaac don’t-” One of the twins cut in, Isaac silencing them with a wave of his hand, his eyes locked on Stiles. It made Stiles skin itch, the intense gaze seeming to bore into him.

“Well?”

“Uh, lots of space, a nice kitchen that I can actually cook in. A deck or a balcony would be sweet. A pool would be pretty awesome too, the real selling point would be a library.” Stiles responds hesitantly, staring back at the taller man in confusion.

“We gotta go, Laura just texted me the address.” One of the twins, Stiles still doesn’t know their names, says as he checks his phone, looking strangely relieved at the chance to leave.

“Nice chatting with you, it’s been fun Stiles.” Isaac smirks as he stands, throwing a few bills onto countertop before following the twins out of the bar.

“That was weird.” Stiles mutters, getting a nod from Jackson as he collects the money.

“Shit, he left like 200 dollars.” Jackson whistles before stuffing the money into the tip jar near the register.

“Really weird.” Stiles mumbles with a shake of his head.

Story of his life, right?

 

 

 

***

 

 

 

It’s been almost two weeks since the clothes were dropped off at his door. Nothing else had shown up since, no letters, no money, no anything and Stiles isn’t sure what to make of the situation. Work has been tiring, his days off spent sleeping as much as possible to make up for the 20 hour days he has. Stiles had talked to his dad earlier in the week who had offered to send Stiles money so he could cut back on his hours but Stiles had refused. He didn’t want his dad to have to pick up even more time at work just to send Stiles money.

Jackson and he had been working more and more together, getting along pretty well even if their personalities clash every now and again. Jackson always made a point to educate Stiles on who he was wearing and how much it cost whenever he wore one of the outfits D had bought him, teasing Stiles about his sugar daddy whenever he could.

Jackson had also teamed up with Erica and was trying to set Stiles up on dates, much to his annoyance. Sure he would like to get a little action but he wasn’t looking for anything right now, not with his work schedule. He barely had enough time to sleep during the week, let alone go on a date. Stiles couldn’t even find it in himself to take someone home for the night, too tired when he closed up the bar to even think about sex.

Today was his first day off at the diner, having Wednesday, Friday, and Sunday off this week much to his overworked body’s pleasure. His shift at the bakery had gone by quickly and Erica had taken his shift at the bar tonight meaning he had a whole 18 hours off that he planned to sleep most of which away.

Stiles stripped down to his boxers the second he got into his room, throwing the flour coated t-shirt and jeans into the laundry basket and face planting onto the bed, knocking out in seconds.

Stiles is awoken five hours later when his stomach starts to rumble and his bladder on the verge of exploding. He relieves himself quickly before he makes his way into the kitchen to fix himself a sandwich and some soup. Stiles eats in silence, scrolling through his Facebook feed and setting a reminder to register himself for classes later on.

Once he had finished off the last of his soup he sets the bowl in the sink and pulls on a pair of old sweatpants to go down and get the mail, stopping in his tracks when he gets to the front door and sees the yellow envelope sitting on the floor. Stiles, feeling lazy, sits down on the hardwood floor and grabs the envelope, hearing a soft jingle inside that makes him frown in thought.

“What the fuck?” Stiles breaths when he opens the package, a note, a small stack of papers and a pair of shiny new keys sitting on the floor where he had dumped them.

_‘A little birdy told me you wanted a library and a nice kitchen, hope this is up to your standards. -D’_

There’s an address printed on the bottom of the note. The stack of papers is a lease packet that is filled out and waiting for his signature. According to the papers it’s paid in full and complete furnished.

“No fucking way.” Stiles hisses at the document, pulling out his phone and googling the [address](https://www.zillow.com/homedetails/18427-Tudor-Rd-Jamaica-NY-11432/32080694_zpid/?fullpage=true) quickly. Stiles almost has a panic attack looking at the price, his heart pounding in his chest as he clicks through the pictures.

“No. Fucking. Way.” Stiles repeats, grinding his teeth together as he shuts his eyes trying to get his heart to stop beating so hard. A random stranger did not just buy him a 4 million dollar house in Queens. There’s no fucking way in Hell this is actually happening.

“Who needs that many fucking bedrooms? _Who_! This is not fucking happening, this is some stupid ass joke. There’s no way-” Stiles cuts himself off, pushing off the floor in anger and running into the bedroom to throw on a pair of jeans and a t-shirt quickly. Slipping into his converse and grabbing his wallet, shoving it in his pocket and head for the door.

He collects the keys and lease for the house before he leaves, locking up his apartment and flagging down a cab when he hits the curb. Stiles gives the address to the driver, his hands balled into fists as he tries to keep himself from fidgeting in his seat. Stiles was just going to go check if this really was some elaborate joke or not. Just for some peace of mind.

They arrive in far less time than Stiles thought it would take, the cabbie pulling up in front of the house with raised eyebrows. Stiles thanks him quickly as he pays the fair, scrambling out of the backseat and then just standing there in the middle of the driveway staring up at the house. It looks just like the picture, the tan brick standing two stories tall, windows lining the majority of the front and a set of wooden double doors leading inside.

“Fucking hell,” Stiles mutters to himself as he makes his way up the five short steps to the doors, his hands shaking slightly as he slides the key into the lock and twists. It opens. The key actually works.

“Holy hell, okay okay.” Stiles whispers as he pushes the door open, perfect white walls and polished hardwood floors greeting him. Stiles takes a cautious step inside, letting the door slide shut behind him as he takes in his surroundings with wide eyes. They’re a staircase down the hall, a dining room to his right and the living room is to his left, a beautiful grand piano in the corner. Stiles takes a step towards it, freezing when he sees the figure sitting on the large white couch in the middle of the room.

The man’s back is to him, his leather-clad arms thrown over the back of the couch as he stares into the glowing fireplace.

“Um,” Stiles begins to say, his words dying in his throat when the man turns his head, multi-colored eyes, manly stubble, and pretty pink smiling lips over cute little bunny teeth greeting him.

“Hello Stiles,” The man smiles, standing gracefully from the couch and turning fully to face him.

 _‘There’s a God sitting in the house a stranger bought me.’_ Stiles thinks to himself as he takes in the man in front of him.

He tall, maybe an inch or two taller than Stiles himself, dark hair gelled to perfection and stubble to match. The man is built, his shoulders wide and his arms straining against his leather jacket. A tight grey henley and black jeans that look painted on his strong legs. Stiles thinks he might be dreaming, maybe the last few months he’s actually been in a coma and he’s making all of this up in his head. He even counts his fingers to check, coming up with ten somehow.

“Are you my sugar daddy?” Stiles blurts out, slapping a hand over his mouth when his brain catches up to his mouth. The man lets out a soft laugh, making his way around the couch till he’s standing just feet away from Stiles. Stiles can smell his cologne from here, it smells heavenly, Stiles kinda wants to bury his face into the guy's chest so he can figure out exactly what it is.

“If that’s what you’d like to call it.” The man smiles, Stiles doesn’t think he should be allowed to smile like that. All soft and gorgeous and way too pretty to be legal. He’s still not convinced any of this is real.

“Why? I mean, why did you send me all that stuff? How’d you even know I needed anything? I don’t even know your name.” Stiles questions, he needs answers damn it, the grass could be fucking purple right now and it would make more sense than his life does.

“It’s Derek and I found your wallet outside of the bar, did some digging and saw how much you were struggling to get by, since I have more than enough money, I thought I’d lend a hand.” The man, Derek, shrugs in reply.

“So you just decided to send me 15,000 dollars, a cloud, and a new designer wardrobe? Oh yeah, and buy me a fucking house? Who does that?” Stiles waves his hands around, a little pissed off but mostly really fucking confused. His life, seriously.

“You caught my interest, which isn’t an easy thing to do.” Derek answers, leaning back on the couch, his arms crossed over his chest. No one should look that good in leather, no one.

“How did you know I needed a new bed? Or what I wanted in a house?” Stiles questions, ignoring that interesting bit of information for the time being as he takes a few steps closer to Derek, his eyebrows lifted in question.

“A friend of mine, Isaac, has been keeping tabs for me. Told me about your conversations with the girl you work with.” Derek admits, not even looks ashamed that he had someone spying on Stiles. Stiles should probably be more alarmed by that fact. He isn’t because he has no self-preservation skills apparently.

“Okay, let's pretend for a second that’s not seven layers of weird, why the house?”

Derek actually had the decency to look sheepish at the last part, his ears turning a light shade of red that Stiles did not find adorable, nope. Definitely not.

“Isaac said-well he told me about what you wanted in life and I thought why not let you have it.”

“ _Oh my God_ , you have a crush on me! I told him if you bought me a house and paid off my student loans I’d marry you no questions asked! You totally want to have my babies!” Stiles cries, his eyes wide as he connects the dots, feeling a little like an idiot but also incredibly smug that someone like Derek actually wanted him, would buy him a ridiculously huge house with way too many bedrooms just to impress him.

“You’re ridiculous, but I did pay off your loans.” Derek huffs, a small smile playing on his rudely attractive face.

“How in the fuck-what do you _do_ for a living?”

Derek doesn’t look that much older, maybe early thirties if Stiles had to guess. He didn’t understand how the guy could just drop 4 million dollars on a house for someone he had a crush on through. Didn’t understand how this guy could even like him, but hey, don’t look a gift horse in the mouth, right?

Derek doesn’t say anything at first, his eyes running over Stiles’ face like he was searching for something, he starts speaking so he must have found it.

“Have you heard of the Blood Wolves?” Derek questions, making Stiles’ eyes widen in shock and understanding.

“My sugar daddy is in the mob, holy shit, this explains so much.” Stiles whispers, more to himself than to Derek. Stiles really shouldn’t find that information so attractive, the Blood Wolves were the biggest crime family in the state. Ruthless and meticulous and overall scary as fuck if you got on their bad side. They were apparently also generous as hell and had no idea how to act like normal people do when they have a crush. Stiles doesn’t really have a lot of room to talk though, not after pining for (stalking) Lydia Martin for the better part of 7 years.

“Is that a problem?” Derek looks like he’s ready for Stiles to storm out of the house and turn him into the police, his shoulders tense and his face expressionless. Stiles isn’t having it.

“In this economy? I’m just going to politely thank you and ask if there are any job openings, can’t have you paying for me the rest of my life. Relationships are all about being equals.” Stiles states, biting back a grin when Derek’s shoulders sag and his eyes start to shine with the smallest bit of hope.

“Relationship?” Derek repeats softly, pushing off the couch as Stiles takes two more steps towards him.

“I _did_ promise my hand in marriage, but maybe we can try dating first. We’re going to have a long conversation about proper social skills though, yours need some work.” Stiles nods, his words teasing as he comes to stand just inches in front of Derek.

“You want to date?” Derek asks, his face full of surprise. Stiles gets it, they don’t know each other, have only communicated between notes and Isaac spying on him. Stiles never claimed to be a rational person though. He's just going to see where this takes him.

“I mean, I did just get this new house with way too many bedrooms, it’d be nice to share it with someone. I’ll even let you test out this sweet new bed I got,” Stiles smirks back, resting a hand on the other man’s shoulder.

“You’re crazy,” Derek states, smiling happily as he says it. Stiles thinks that a good start, laying out all fundamentals of each other’s character.

“Maybe, but I’m not the one who’s been sending expensive ass gifts to the broke college student I’m crushing on because I don’t know how to ask someone on a date.” Stiles fires back.

“You would have said no, you’re always working, you barely sleep.” Derek defends, his hands reaching out to hold Stiles by the waist. Stiles is very much on board with that development.

“Got rid of that problem for me, didn’t you? Now, what do you say you give me a tour of my new house, starting with the bedroom would be in your best interest.” Stiles hums, their faces only an inch apart. Stiles was pretty sure God had spent extra long time on making Derek’s eyes look like that. They were breathtaking.

“I think I can manage that.” Derek whispers back, sending a shiver down Stiles’ spine with the husky tone coating each word. Stiles can’t help himself anymore, surging forward to crash his lips against Derek in a ferise exchange of tongue and messy kisses.

“So, is the sugar daddy title limited to you buying me things _or_?” Stiles breathes out when they finally break away for air, pulling a broken groan from the older man. Stiles is going to assume that means Derek might be into it.

“You’re going to be the death of me.” Derek accuses hotly as he pulls Stiles off his feet, both hands cupping his ass, Stiles’ legs wrapping around his waist and his arms around his neck. Stiles hums in approval, his teeth nibbling on the warm skin under Derek’s ear as the man starts for the stairs.

“Probably, I’m worth it though, promise.”

“I don’t doubt that,” Derek hums, giving Stiles’ ass a firm squeeze.

“So when do I get to pledge my loyalty to the mob?”

 

 

 

**Author's Note:**

> Hope you like it, let me know what you think and if you know any good prompts send them my way :)


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